4-(5-Fluoro-2-methoxy-phenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal → 5-[4-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylidenamino]quinoline-2-carboxylic acid diethylamide

HRID 2215459Notes

Reaction equation

HRID 2215459 reaction equation
[CH2:1]([N:3]([CH2:17][CH3:18])[C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[NH2:16])[N:7]=1)=[O:5])[CH3:2].[F:19][C:20]1[CH:21]=[CH:22][C:23]([O:38][CH3:39])=[C:24]([C:26]([CH3:37])([CH3:36])[CH2:27][C:28]([OH:35])([C:31]([F:34])([F:33])[F:32])[CH:29]=O)[CH:25]=1>O1CCCC1.[Ti]>[CH2:17]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[N:16]=[CH:29][C:28]([OH:35])([C:31]([F:32])([F:34])[F:33])[CH2:27][C:26]([C:24]2[CH:25]=[C:20]([F:19])[CH:21]=[CH:22][C:23]=2[O:38][CH3:39])([CH3:36])[CH3:37])[N:7]=1)=[O:5])[CH3:18]

Participants

5

Reactant 2

HCID 115731224-(5-Fluoro-2-methoxy-phenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanalHCID 69203919HCID 69203919, compound

Product 1

HCID 692051715-[4-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylidenamino]quinoline-2-carboxylic acid diethylamide

Reagents, catalysts & solvents 2

HCID 23963TitaniumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution that consists of 210 mg (0.86 mmol) of 5-aminoquinoline-2-carboxylic acid diethylamide, 266 mg (0.86 mmol) of 4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal and 0.36 ml (1.73 mmol) of titanium tetraethylate in 15 ml of tetrahydrofuran is stirred for one hour at room temperature and then for 3 hours at 80° C. After removal of the solvent and purification on silica gel with hexane-ethyl acetate (0–70%), 230 mg (52% of theory) of the product is obtained.

Workup

  1. waitfor 3 hours at 80° C
  2. customAfter removal of the solvent and purification on silica gel with hexane-ethyl acetate (0–70%), 230 mg (52% of theory) of the product
  3. customis obtained

Sources & evidence

ORD record
ord-24096dcbdb934fed9cec4a01ccf947af
Source dataset
uspto-grants-2006_09
Patent number
US07109212B2

Reaction notes

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